#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/47/2214765.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2214765
loop_
_publ_author_name
'Yang-Gen Hu'
'Yu-Lu Chen'
'Ting Xie'
'Ming-Guo Liu'
_publ_section_title
3-Phenyl-2-(pyrrolidin-1-yl)-6,7-dihydro-5H-cyclopenta[b]thieno[5,4-d]pyrimidin-4(3H)-one
_journal_coeditor_code           IS2190
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3474
_journal_page_last               o3475
_journal_paper_doi               10.1107/S160053680703365X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C19 H19 N3 O S'
_chemical_formula_moiety         'C19 H19 N3 O S'
_chemical_formula_sum            'C19 H19 N3 O S'
_chemical_formula_weight         337.43
_chemical_name_systematic
;
3-Phenyl-2-(pyrrolidin-1-yl)-6,7-dihydro-
5H-cyclopenta[b]thieno[5,4-d]pyrimidin-4(3H)-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.503(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.094(3)
_cell_length_b                   8.5709(10)
_cell_length_c                   17.271(2)
_cell_measurement_reflns_used    3147
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      25.83
_cell_measurement_theta_min      2.37
_cell_volume                     3408.0(7)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0954
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12733
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+2.2147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1364
_refine_ls_wR_factor_ref         0.1534
_reflns_number_gt                2613
_reflns_number_total             3323
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2190.cif
_cod_data_source_block           I
_cod_original_cell_volume        3408.1(7)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2214765
_cod_database_fobs_code          2214765
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.39367(11) -0.0658(3) 0.13067(14) 0.0543(6) Uani d . 1
C C2 0.41197(13) -0.2289(4) 0.15237(19) 0.0809(9) Uani d . 1
H H2A 0.3879 -0.3051 0.1235 0.097 Uiso calc R 1
H H2B 0.4099 -0.2471 0.2075 0.097 Uiso calc R 1
C C3 0.47452(15) -0.2359(5) 0.1303(2) 0.1023(12) Uani d . 1
H H3A 0.4770 -0.3026 0.0853 0.123 Uiso calc R 1
H H3B 0.4994 -0.2790 0.1729 0.123 Uiso calc R 1
C C4 0.49430(14) -0.0708(5) 0.1119(2) 0.1030(13) Uani d . 1
H H4A 0.5214 -0.0306 0.1528 0.124 Uiso calc R 1
H H4B 0.5121 -0.0673 0.0629 0.124 Uiso calc R 1
C C5 0.43829(11) 0.0173(3) 0.10746(16) 0.0630(7) Uani d . 1
C C6 0.34115(9) 0.0224(2) 0.12941(13) 0.0442(5) Uani d . 1
C C7 0.34809(9) 0.1721(3) 0.10331(13) 0.0442(5) Uani d . 1
C C8 0.28480(9) -0.0255(2) 0.14761(13) 0.0420(5) Uani d . 1
C C9 0.25506(9) 0.2454(2) 0.11414(12) 0.0380(5) Uani d . 1
C C10 0.16339(9) 0.3712(2) 0.15540(14) 0.0477(6) Uani d . 1
H H10A 0.1720 0.3276 0.2068 0.057 Uiso calc R 1
H H10B 0.1291 0.3206 0.1309 0.057 Uiso calc R 1
C C11 0.15533(11) 0.5480(2) 0.15893(16) 0.0573(7) Uani d . 1
H H11A 0.1152 0.5750 0.1656 0.069 Uiso calc R 1
H H11B 0.1801 0.5934 0.2010 0.069 Uiso calc R 1
C C12 0.17302(11) 0.6016(2) 0.08106(16) 0.0559(6) Uani d . 1
H H12A 0.1814 0.7125 0.0813 0.067 Uiso calc R 1
H H12B 0.1431 0.5791 0.0400 0.067 Uiso calc R 1
C C13 0.22717(10) 0.5061(2) 0.07185(14) 0.0498(6) Uani d . 1
H H13A 0.2340 0.4931 0.0175 0.060 Uiso calc R 1
H H13B 0.2610 0.5541 0.0988 0.060 Uiso calc R 1
C C14 0.18283(9) 0.0414(2) 0.14200(13) 0.0399(5) Uani d . 1
C C15 0.16433(11) -0.0078(3) 0.21238(15) 0.0542(6) Uani d . 1
H H15 0.1890 -0.0014 0.2575 0.065 Uiso calc R 1
C C16 0.10902(13) -0.0664(3) 0.2147(2) 0.0689(8) Uani d . 1
H H16 0.0962 -0.0998 0.2616 0.083 Uiso calc R 1
C C17 0.07258(12) -0.0756(3) 0.1479(2) 0.0726(9) Uani d . 1
H H17 0.0353 -0.1159 0.1496 0.087 Uiso calc R 1
C C18 0.09132(11) -0.0254(3) 0.07868(19) 0.0634(7) Uani d . 1
H H18 0.0663 -0.0298 0.0338 0.076 Uiso calc R 1
C C19 0.14687(10) 0.0317(2) 0.07496(15) 0.0482(6) Uani d . 1
H H19 0.1598 0.0632 0.0277 0.058 Uiso calc R 1
N N1 0.24184(7) 0.09507(17) 0.13812(10) 0.0381(4) Uani d . 1
N N2 0.30734(8) 0.28498(19) 0.09507(11) 0.0443(4) Uani d . 1
N N3 0.21341(7) 0.35543(18) 0.10766(10) 0.0402(4) Uani d . 1
O O1 0.27071(7) -0.15575(17) 0.16791(11) 0.0606(5) Uani d . 1
S S1 0.41935(3) 0.20650(8) 0.08088(5) 0.0691(3) Uani d . 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 C1 C6 112.7(2)
C5 C1 C2 111.2(2)
C6 C1 C2 136.0(2)
C1 C2 C3 103.2(3)
C1 C2 H2A 111.1
C3 C2 H2A 111.1
C1 C2 H2B 111.1
C3 C2 H2B 111.1
H2A C2 H2B 109.1
C2 C3 C4 108.7(2)
C2 C3 H3A 110.0
C4 C3 H3A 110.0
C2 C3 H3B 110.0
C4 C3 H3B 110.0
H3A C3 H3B 108.3
C5 C4 C3 102.0(3)
C5 C4 H4A 111.4
C3 C4 H4A 111.4
C5 C4 H4B 111.4
C3 C4 H4B 111.4
H4A C4 H4B 109.2
C1 C5 C4 113.5(3)
C1 C5 S1 113.14(18)
C4 C5 S1 133.3(2)
C7 C6 C8 118.32(18)
C7 C6 C1 112.3(2)
C8 C6 C1 129.4(2)
N2 C7 C6 127.3(2)
N2 C7 S1 121.15(17)
C6 C7 S1 111.55(16)
O1 C8 C6 126.57(19)
O1 C8 N1 119.61(19)
C6 C8 N1 113.80(17)
N2 C9 N3 117.44(18)
N2 C9 N1 122.49(17)
N3 C9 N1 120.04(18)
N3 C10 C11 102.49(17)
N3 C10 H10A 111.3
C11 C10 H10A 111.3
N3 C10 H10B 111.3
C11 C10 H10B 111.3
H10A C10 H10B 109.2
C12 C11 C10 102.94(18)
C12 C11 H11A 111.2
C10 C11 H11A 111.2
C12 C11 H11B 111.2
C10 C11 H11B 111.2
H11A C11 H11B 109.1
C11 C12 C13 102.31(18)
C11 C12 H12A 111.3
C13 C12 H12A 111.3
C11 C12 H12B 111.3
C13 C12 H12B 111.3
H12A C12 H12B 109.2
N3 C13 C12 102.83(18)
N3 C13 H13A 111.2
C12 C13 H13A 111.2
N3 C13 H13B 111.2
C12 C13 H13B 111.2
H13A C13 H13B 109.1
C19 C14 C15 120.9(2)
C19 C14 N1 119.35(19)
C15 C14 N1 119.6(2)
C16 C15 C14 119.2(3)
C16 C15 H15 120.4
C14 C15 H15 120.4
C15 C16 C17 120.3(3)
C15 C16 H16 119.8
C17 C16 H16 119.8
C18 C17 C16 119.9(2)
C18 C17 H17 120.1
C16 C17 H17 120.1
C17 C18 C19 120.7(3)
C17 C18 H18 119.7
C19 C18 H18 119.7
C14 C19 C18 119.0(2)
C14 C19 H19 120.5
C18 C19 H19 120.5
C9 N1 C8 122.32(17)
C9 N1 C14 122.50(16)
C8 N1 C14 114.33(15)
C9 N2 C7 115.67(18)
C9 N3 C13 118.14(17)
C9 N3 C10 127.09(18)
C13 N3 C10 110.91(15)
C5 S1 C7 90.33(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C5 1.340(4)
C1 C6 1.428(3)
C1 C2 1.499(3)
C2 C3 1.524(4)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.528(5)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C5 1.495(3)
C4 H4A 0.9700
C4 H4B 0.9700
C5 S1 1.732(3)
C6 C7 1.373(3)
C6 C8 1.423(3)
C7 N2 1.350(3)
C7 S1 1.745(2)
C8 O1 1.222(3)
C8 N1 1.433(2)
C9 N2 1.321(3)
C9 N3 1.345(2)
C9 N1 1.395(2)
C10 N3 1.477(3)
C10 C11 1.528(3)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C12 1.507(4)
C11 H11A 0.9700
C11 H11B 0.9700
C12 C13 1.514(3)
C12 H12A 0.9700
C12 H12B 0.9700
C13 N3 1.477(3)
C13 H13A 0.9700
C13 H13B 0.9700
C14 C19 1.373(3)
C14 C15 1.385(3)
C14 N1 1.445(3)
C15 C16 1.376(4)
C15 H15 0.9300
C16 C17 1.376(4)
C16 H16 0.9300
C17 C18 1.372(4)
C17 H17 0.9300
C18 C19 1.379(3)
C18 H18 0.9300
C19 H19 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C10 H10A O1 4_555 0.97 2.45 3.309(3) 148
C10 H10B Cg5 1_555 0.97 2.90 3.429(2) 115
C12 H12A Cg5 1_565 0.97 2.89 3.630(2) 134
C12 H12B Cg1 7_555 0.97 2.93 3.790(3) 148
C13 H13A Cg4 7_555 0.97 2.67 3.542(3) 150
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C5 C1 C2 C3 -5.6(3)
C6 C1 C2 C3 175.2(3)
C1 C2 C3 C4 10.9(4)
C2 C3 C4 C5 -11.9(4)
C6 C1 C5 C4 177.3(3)
C2 C1 C5 C4 -2.1(4)
C6 C1 C5 S1 -1.1(3)
C2 C1 C5 S1 179.5(2)
C3 C4 C5 C1 8.7(4)
C3 C4 C5 S1 -173.2(3)
C5 C1 C6 C7 1.1(3)
C2 C1 C6 C7 -179.7(3)
C5 C1 C6 C8 178.0(2)
C2 C1 C6 C8 -2.8(5)
C8 C6 C7 N2 2.7(4)
C1 C6 C7 N2 180.0(2)
C8 C6 C7 S1 -177.87(16)
C1 C6 C7 S1 -0.5(3)
C7 C6 C8 O1 176.4(2)
C1 C6 C8 O1 -0.4(4)
C7 C6 C8 N1 -1.9(3)
C1 C6 C8 N1 -178.7(2)
N3 C10 C11 C12 33.1(2)
C10 C11 C12 C13 -43.4(2)
C11 C12 C13 N3 36.1(2)
C19 C14 C15 C16 -0.3(3)
N1 C14 C15 C16 -176.64(19)
C14 C15 C16 C17 -0.1(3)
C15 C16 C17 C18 -0.4(4)
C16 C17 C18 C19 1.3(4)
C15 C14 C19 C18 1.2(3)
N1 C14 C19 C18 177.51(18)
C17 C18 C19 C14 -1.7(3)
N2 C9 N1 C8 3.2(3)
N3 C9 N1 C8 -178.62(18)
N2 C9 N1 C14 -165.56(19)
N3 C9 N1 C14 12.6(3)
O1 C8 N1 C9 -179.2(2)
C6 C8 N1 C9 -0.8(3)
O1 C8 N1 C14 -9.5(3)
C6 C8 N1 C14 168.88(18)
C19 C14 N1 C9 63.7(2)
C15 C14 N1 C9 -119.9(2)
C19 C14 N1 C8 -106.0(2)
C15 C14 N1 C8 70.4(2)
N3 C9 N2 C7 179.18(19)
N1 C9 N2 C7 -2.6(3)
C6 C7 N2 C9 -0.3(3)
S1 C7 N2 C9 -179.74(15)
N2 C9 N3 C13 6.6(3)
N1 C9 N3 C13 -171.66(18)
N2 C9 N3 C10 -149.2(2)
N1 C9 N3 C10 32.6(3)
C12 C13 N3 C9 -175.30(18)
C12 C13 N3 C10 -15.8(2)
C11 C10 N3 C9 146.5(2)
C11 C10 N3 C13 -10.7(2)
C1 C5 S1 C7 0.7(2)
C4 C5 S1 C7 -177.4(3)
N2 C7 S1 C5 179.4(2)
C6 C7 S1 C5 -0.06(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21123830
2 PubChem 139072740
